21211-22-3Relevant articles and documents
An efficient route to regioselective functionalization of benzo[b]thiophenes via palladium-catalyzed decarboxylative Heck coupling reactions: Insights from experiment and computation
Yang, Daoshan,Liu, Yuxia,Sun, Pengfei,Zhang, Ning,Wei, Wei,Sun, Mingyang,Chen, Guang,Bi, Siwei,Wang, Hua
, p. 895 - 904 (2016)
Pd-catalyzed decarboxylative Heck-type coupling of 3-chlorobenzo[b]thiophene-2-carboxylic acids with styrenes have been developed as an efficient strategy for the construction of functionalized benzo[b]thiophenes. Theoretical analysis shows that AgCl generated during the reaction, instead of Pd, π-coordinates with the carboxyl O atom, making easy the rate-determining CO2 dissociation. The divergent reactivities of the Cl-substituted and H-substituted 3-benzo[b]thiophene-2-carboxylic acids are mainly due to the presence of the Cl substituent, which reduces the adjacent π-π interplay, thereby significantly contributing to decarboxylation. Therefore, the presence of both AgCl and the Cl substituent are of key importance in ensuring the occurrence of the reaction under the given conditions.
Synthesis, characterization and biological activities of some new benzo[b]thiophene derivatives
Isloor, Arun M.,Kalluraya, Balakrishna,Sridhar Pai
body text, p. 825 - 830 (2010/04/04)
Benzo[b]thiophene molecules are found to be important tools in synthetic medicinal chemistry. They are of current interest due to their wide spectrum of pharmacological properties. In view of the biological activities of benzo[b]thiophene containing molecules, in this present research work, we propose the synthesis of some new benzo[b]thiophene derivatives such as thiadiazoles, oxadiazoles, pyrazolin & diaryl pyrazoles starting from 3-chlorobenzo[b]thiophene-2-carboxyl chloride. These newly synthesized compounds were characterized by elemental analyses, I.R, NMR and Mass spectral studies. Some of the selected compounds were screened for their antibacterial, antifungal and anti-inflammatory studies. Many of the molecules were found to be potent.
SYNTHESIS AND SOME TRANSFORMATIONS OF BENZOTHIOPHENE DERIVATIVES
Sidorenko, T.N.,Terent'eva, G.A.,Raida, V.S.,Andrienko, O.S.,Savinykh, Yu.V.,Aksenov, V.S.
, p. 1246 - 1250 (2007/10/02)
A number of 3-chloro-2-chlorocarbonylbenzothiophenes with alkyl substituents in various positions of the benzene ring were synthesized by arylation of acrylic acid with the corresponding alkyl-substituted iodobenzenes under the influence of catalytic amounts of palladium acetate and subsequent oxidation of the resulting arylacrylic acids with thionyl chloride.Replacement of the pyridine added in the oxidation reaction by triethylbenzylammonium chloride led to substantial increases in the yields of the desired products.The possibility of conversionof the resulting benzothiophene derivatives to thiophene ring-unsubstituted benzothiophenes was shown in the case of 3-chloro-2-chlorocarbonylbenzothiophene as a result of successive saponification of the 2-chlorocarbonyl group, decarboxylation, and dechlorination.
